Classifications

• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
  • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
  • A01N37/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the group; Thio analogues thereof

Definitions

• the invention herein pertains to the field of herbicides.
• the invention pertains to the field of herbicides suitable for use against undesired vegetation in the presence of transplanted rice.
• this invention pertains to the preemergent or postemergent use of N-(butoxymethyl)-640 -tert-butyl-2-chloro-o-acetotoluidide against monocotyledonous and dicotyledonous weeds, e.g., grasses, sedges and broadleaf weeds, in the presence of transplanted rice.
• the food crop rice is the major food staple for approximately 60% of the world's population. This crop is grown on an estimated 326 million acres (about 131.9 million hectares). Of the total rice coverage under cultivation, it is estimated that 70%, or about 229 million acres (about 92.7 million hectares), is the transplanted rice culture, and the remaining 30%, or about 97 million acres (about 39.3 million hectares), is the direct-seeded rice culture (including drill-seeded, broadcastsown, puddle-seeded, water-seeded and upland). Accordingly, much effort is required to produce sufficient rice to meet the widespread demand therefor.
• N-oxaalkylene- ⁇ -haloacetanilides are those wherein the positions ortho to the anilide nitrogen atom are both unoccupied by any substituents, or one or both ortho positions are occupied by various radicals including straight or branched-chain alkyl radicals, and the oxaalkylene substituent on the anilide nitrogen atom has one or more carbon atoms in the alkylene moiety adjacent to the nitrogen atom.
• oxaalkylene is meant an alkylene radical one of whose methylene groups has been replaced with an oxa oxygen atom (--O--) resulting in a radical of the structure --CH 2 --O--CH 2 --.
• ⁇ -haloacetanilide herbicidal compounds of the above types are such compounds as are described in U.S. Pat. Nos. 2,863,752, 3,442,945, 3,547,620, 3,663,200 and British Pat. No. 1,008,851, all of which are assigned to applicant's assignee herein.
• the ortho positions may be both occupied by hydrogen atoms or one of these positions may be occupied with, inter alia, an alkyl radical having up to four carbon atoms.
• 1,008,851 discloses N-oxaalkylene compounds wherein one of the ortho positions may be an alkyl group and the other ortho position must be occupied by a tert-alkyl group.
• Both of said U.S. '752 and British '851patents exemplify the above types of compounds with no less than two alkylene carbon atoms in the oxaalkylene moiety of the compounds.
• neither of the '752 nor '851 patents disclose any herbicidal utility with respect to rice of any culture.
• the application rate use requirements are from 3 to 6 (or more) times less, and (2) the time span of application to the weeds is much greater, i.e., the compound of this invention may be effectively applied as late as the 2-2.5 leaf stage of growth, whereas butachlor is applied at the 1 leaf stage of growth to achieve optimum weed control.
• Example 4 As shown in Table I of each of said '620 and '945 patents, the compound of Example 4 therein exhibited severe phytotoxicity with respect to direct-seeded rice plants under the conditions of the test and at the concentrations used, i.e., 1.0 lb/ac (ca. 1.12kgs/ha) and 0.25 lb/ac (ca. 0.28 kg/ha). Accordingly, that disclosure standing alone would tend to suggest to those skilled in the art that the compound of said Example 4 would be unsatisfactory for use as a rice herbicide, at least, at the rates tested.
• the present invention relates to a method for selectively inhibiting (including complete control of) certain undesirable vegetation in the presence of transplanted rice.
• the method of this invention comprises applying to the growth medium of and/or said undesirable vegetation and transplanted rice a herbicidally effective amount of the compound N-(butoxymethyl)-6'-tert-butyl-2-chloro-o-acetotoluidide.
• Undesirable vegetation against which said compound has shown results ranging from fair to excellent control includes monocotyledons and dicotyledons such as grasses, sedges and broadleaf weeds.
• grasses effectively treated to date are the following: Brachiaria platyphylla, Digitaria spp, Echinochloa spp, Eleusine indica, Leptochloa spp and Setaria spp.
• Cyperus difformis Cyperus iria
• Cyperus serotinus Eleocharis acicularis
• Eleocharis kuroguwai Fimbristylis spp
• Scirpus hotarui Scirpus spp (bulrush).
• the herbicide according to this invention is applied at rate corresponding to from about 0.05 lb/acre to about 4 or more lbs/acre (about 0.06 kg/hectare to about 4.58 kgs/hectare or more).
• Preferred application rates range from about 0.25 to 1.5 lbs/acre (i.e., from about 0.28 to about 1.68 kgs/hectare).
• the most preferred application rate is about 0.5 lb/acre (about 0.56 kg/hectare).
• the herbicide of this invention can be applied preemergently (i.e., with respect to emergence of undesired vegetation), both by incorporation into the soil or by application to the surface thereof, or to the surface of the water into which the rice seedlings are transplanted, or postemergently, i.e., in direct contact with said undesired vegetation.
• N-(butoxymethyl)-6'-tert-butyl-2-chloro-o-acetotoluidide has superior herbicidal activity with respect to undesired vegetation in the presence of transplanted rice with negligible crop injury, i.e., a high degree of crop safety at recommended use rates.
• a concomitant result of achieving the above objectives is increased economy based on use of less herbicide to control weeds.
• the present invention is exemplified herein by tests in laboratory-greenhouse investigations and by field tests in countries in which transplanted rice is a major crop, i.e., Japan, Republic of Korea, Taiwan and the Philippine Islands. Results of such tests are presented in the tables below.
• the said active ingredients are prepared by reacting the appropriate substituted methylene aniline with chloroacetyl chloride to produce the corresponding N-chloromethyl- ⁇ -chloroacetanilide intermediate product which is then reacted with n-butanol to produce the final product.
• the herbicides were formulated and used in granular form in conventional manner.
• the granular herbicide embodiment of this invention comprised 2.5% active ingredient (i.e., N-(butoxymethyl)-6'- tert-butyl-2-chloro-o-acetotoluidide), 95.24% clay (calcined attapulgite), 2.0% dipropylene glycol as stabilizer and the balance inert material.
• the commercial herbicide used was a granular product having 5% active ingredient.
• the rice seedlings were grown in conventional manner, by seeding the rice in a typical seedbed of sandy loam to clay soil of the country wherein the test was conducted.
• the seedlings were obtained by seeding rice in a mixture of soil, e.g., Ray silt loam, and peat in wood flats.
• the rice was usually allowed to grow for 6-15 days before lifting for transplanting. Older (ordinary) rice plants were usually grown for a period of about 2-3 weeks, or as much as about 7 weeks before lifting.
• n-(butoxymethyl)-6'-tert-butyl-2-chloro-o-acetotoluidide (the compound of use in this invention).
• Herbicide A was many times (usually at least 4 or 5 times) more active than Herbicide B.
• perenniaal control at 14 DAT and at rates less than 2 kgs/ha applied 5 DAT was considered less than adequate, the advantage over Herbicide B is clearly evident.
• control of the perennial EK by Herbicide A has ranged from fair to good, whereas, activity against Sa remains generally weak. The slight early season injury to rice was outgrown.
• Rice seedlings (ordinary) of Tainan No. 5 variety (japonica) were transplanted at 19 days of growth.
• Granular formulations of Herbicides A and B were applied at the 1 leaf stage of grass weed (4 DAT) and 2.5 leaf stage of grass weed (10 DAT). Observations were made at 63 DAT and results reported in Table 2 as an average of 3 replications.
• Herbicide A was 3-6 fold more active and could be applied over a longer period of time than Herbicide B for control of Echinochloa crusgalli and Monochoria vaginalis.
• the latter weed is considered to be the number 1 weed in the first rice crop and the number 2 weed (after Cyperus difformis) in the second rice crop in Taiwan.
• Herbicide A at 2 kgs/ha resulted in a rice yield depression. However, this rate is about 4 times the expected use rate under the conditions prevailing in this example.
• This example sets forth the comparative results of the performance of Herbicides A and B in a field test on Dapog transplanted rice at Munoz, Philippines.
• Herbicide A was applied to the weeds and rice at the indicated times of 2, 7 and 15 DAT, respectively, and 7 DAT for Herbicide B.
• the leaf stage of grass weed (lsg) was as follows: 2 DAT (0-1 1sg), 7 DAT (1-1.5 1sg) and 15 DAT (2-2.5 1sg).
• the weed symbol "Obw” represents "other broadleaf weeds" of unspecified identity. Results presented in Table 5 represent the average of 2 replications.
• Herbicide A was at least 3 fold more active than Herbicide B. Moreover, Herbicide A, at 0.25 kg/ha, applied 2 DAT was equal to or superior to Herbicide B at 1.5 kg/ha applied 7 DAT, on Ec, Ann. Cyp, Obw and in average weed control for both ordinary and infant seedlings and the yields were essentially the same.
• the soil used in these tests was a clay loam with 2.3% organic matter and had a percolation rate of 3 cm/day. Duplicate treatments were used.
• the status of the grass (EC) was as follows:
• Table 6 illustrate an important feature and benefit of Herbicide A, viz., that it may efficaciously be applied over a wide application period, i.e., from 2 days before transplanting to 12 DAT.
• rice seeds and seeds of the weeds shown in Table 7 were sown in Ray silt loam soil at a depth of 0.5 inch (1.27 cm) in containers for the soil in a greenhouse.
• Herbicides A and B were applied to the surface of the soil at a spray volume equivalent to 20 gals/acre (187.1 liters/hectare), followed by 0.5 in (1.27 cm) of overhead irrigation.
• Temperature and relative humidity in the greenhouse were on the order of 85°F (29°C) and 75%, respectively. Observations were made at 21-28 days after seeding.
• Table 7 are shown the average rates of herbicide required to cause a growth reduction of 85% of the weeds ("GR 85 "), and the average rate of herbicide required to cause a growth reduction of 15% (“GR 15 ”) of the rice plants (Oryza sativa, "Os", variety Bluebelle).
• Herbicide A has been found to be significantly more active than Herbicide B.
• the weeds Cc and Ce appear to be resistant to Herbicide A, whereas the Ce weed also resists Herbicide B.
• the second cycle involved the same procedure as the first cycle, except that additionally, the equivalent of 50 lbs/ac (56.05 Kgs/ha) of nitrogen was mixed into the cover layer of the soil which was reseeded with the mixture of plants mentioned earlier.
• the plants were evaluated for herbicidal activity at the end of this six-week period and, again, the soil in which at least 75% of the grasses or broadleaf species or of the sedge alone were controlled was advanced to a third cycle. The foregoing procedure was repeated until herbicidal activity fell below that required for initiation of a new cycle.
• the soil longevity data in Table 9 indicates that Herbicide A would have residual preemergence activity for a period of time about 50% longer than that for Herbicide B when used at equal rates.
• Herbicide A is only about one-half as toxic as Herbicide B with respect to carp. Since the expected use rate of Herbicide A is about one-third that of Herbicide B, and the above fish toxicology data shows Herbicide A to be about one-half as toxic to carp as Herbicide B, then Herbicide A should be only about one-sixth as toxic as Herbicide B in the field.
• Herbicide A has been cleared for use in rice in major rice-growing countries of the world, including, e.g., Taiwan, Japan, Korea, Philippines, Ceylon and other countries.
• Herbicide B has been officially established as the single chemical preemergence rice herbicide standard in Taiwan.
• the herbicidal compositions of this invention comprise the active ingredient and one or more herbicidal adjuvants, which can be solid or liquid extenders, carriers, diluents, conditioning agents and the like.
• herbicidal adjuvants which can be solid or liquid extenders, carriers, diluents, conditioning agents and the like.
• Preferred herbicidal compositions containing the active ingredient of this invention have been developed so that the active ingredients can be used to the greatest advantage to selectively inhibit the growth of undesirable plants, both monocotyledons and dicotyledons, such as sedges, broadleaf weeds and grasses, including barnyardgrass in the presence of transplanted rice.
• the preferred compositions comprise certain wettable powders, aqueous suspensions, dust formulations, granules, emulsifiable oils and solutions in solvents. In general, these preferred compositions can all contain one or more surface-active agents.
• Wettable powders are water-dispersible compositions containing one or more active ingredients, an inert solid extender and one or more wetting and dispersing agents.
• the inert solid extenders are usually of mineral origin such as the natural clays, diatomaceous earth and synthetic minerals derived from silica and silicate. Examples of such extenders include kaolinites, attapulgite clay and synthetic magnesium silicate.
• Preferred wetting agents are alkyl benezene and alkyl naphthalene sulfonates, fulfated fatty alcohols, amines or acid amides; long chain acid esters of sodium isothionate, esters of sodium sulfosuccinate, sulfated or sulfonated fatty acid esters, petroleum sulfonates, sulfonated vegetable oils and detertiary acetylinic glycols.
• Preferred dispersants are methyl cellulose, polyvinyl alcohols, sodium lignin sulfonates, polymeric alkyl naphthalene sulfonates, sodium naphthalene sulfonate, polymethylene bisnaphthalenesulfonate and sodium N-methyl-N-(long chain acid) taurates.
• the wettable powders compositions of this invention usually contain from about 5 to about 95 parts of active ingredient, from about 0.25 to about 3.0 parts of wetting agent, from about 0.25 to about 7 parts of dispersant and from about 4.5 to about 94.5 parts of inert solid extender, all parts being by weight of the total composition. Where required from about 0.1 to 2.0 parts by weight of the solid inert extender can be replaced by a corrosion inhibitor or anti-foaming agent or both.
• Aqueous suspensions are usually prepared by mixing together an aqueous slurry of water-insoluble active ingredient in the presence of dispersing agents to obtain a concentrated slurry of very finely-divided particles.
• the resulting concentrated aqueous suspension is characterized by its extremely small particle size, so that when diluted and sprayed coverage is very uniform.
• Dusts are dense finely-divided particulate compositions which are intended for application to the soil in dry form. Dusts are characterized by their free-flowing and rapid settling properties so that they are not readily wind-borne to areas where they are of no value. Dusts contain primarily an active ingredient and a dense, free-flowing, finely-divided particulate extender. However, their performance is sometimes aided by the inclusion of a wetting agent such as those listed hereinbefore under wettable powder compositions; convenience in manufacture frequently demands the inclusion of an inert, absorptive grinding aid. Suitable class of grinding aids are natural clays, diatomaceous earth and synthetic minerals derived from silica or silicate. Preferred grinding aids include attapulgite clay, diatomaceous silica, synthetic fine silica and synthetic calcium and magnesium silicates.
• the inert finely-divided solid extender for the dusts can be of vegetable or mineral origin.
• the solid extenders are characterized by possessing relatively low surface areas and are poor in liquid absorption.
• Suitable inert solid extenders for herbicidal dusts include micaceous talcs, pyrophyllite, dense kaolin clays, ground calcium phosphate rock and tobacco dust.
• the dusts usually contain from about 0.5 to 99 parts active ingredient, 0 to 50 parts grinding aid, 0 to 3 parts wetting agent and 1 to 99.5 parts dense solid extender, all parts being by weight based on the total weight of the dust.
• the wettable powders described above may also be used in the preparation of dusts. While such wettable powders could be used directly in dust form, it is more advantageous to dilute them by blending with the dense dust diluent. In this manner, dispersing agents, corrosion inhibitors, and anti-foam agents may also be found as components of a dust.
• Emulsifiable oils are usually solutions of active ingredient in water-immiscible solvents together with a surfactant.
• Suitable solvents for the active ingredient of this invention include hydrocarbons and water-immiscible ethers, esters or ketones.
• Suitable surfactants are anionic, cationic and nonionic such as alkyl aryl polyethoxy alcohols, alkyl and alkyl aryl polyether alcohols, polyethylene glycol fatty esters, fatty alkyllol amide condensates, amine salts of fatty alcohol sulfates together with long chain alcohols and oil soluble petroleum sulfonates or mixtures thereof.
• the emulsifiable oil compositions generally contain from about 5 to 95 parts active ingredient, about 1 to 10 parts surfactant and about 4 to 94 parts solvent, all parts being by weight based on the total weight of emulsifiable oil composition.
• Granules are physically stable particulate compositions comprising active ingredient adhering to or distributed through a basic matrix of an inert, finely-divided particulate carrier or extender.
• the surfactant such as those listed hereinbefore under wettable powders can be present in the composition.
• the preferred extenders for use herein are dense, aggregates which are adsorptive for the active ingredient; these include limestone, gypsum, expanded shale, sand and extruded granules. These extenders may be used alone or in admixture with other extenders, e.g., powdered clays.
• extenders include diatomaceous earth, pearlite, volcanic aggregates, natural clays, pyrophyllites, and vermiculite. Preformed and screened particulate attapulgite or heat-expanded vermiculite and the finely-divided clays such as kaolin clays, hydrated attapulgite or bentonitic clays are useful herein. These extenders are sprayed or blended with the active ingredient to form the herbicidal granules.
• the mineral particles which are used in the granular herbicidal compositions of this invention usually have a size range of 10 to 100 mesh, but preferably such that a large majority of the particles have from 14 to 60 mesh with the optimum size being from 16 to 40 mesh. Carriers having substantially all particles between 14 and 80 mesh and at least about 80 percent between 16 and 40 mesh is particularly preferred for use in the present granular compositions.
• the term "mesh" as used herein means U.S. Sieve Series.
• the granular herbicidal compositions of this invention generally contain from about 1 to 30 parts by weight of the active ingredient and about 0 to 5 parts by weight of wetting agent per 100 parts by weight of extender.
• the preferred herbicidal granular compositions contain from about 2 to 25 parts by weight of active ingredient and about 1 to 3 parts by weight of wetting agent per 100 parts by weight of extender.
• the selective herbicidal compositions of this invention can also contain other additaments, for example, fertilizers, other herbicides, pesticides and the like, used as adjuvant or in combination with any of the above-described adjuvants.
• Herbicidally-active compounds which may be used in combination with the compound of this invention include but are not limited to: acetanilides such as butachlor, carbamates such as p-chlorobenzyl diethylthiolcarbamate, benzyl N,N-di-sec-butyl thiolcarbamate and S-ethyl hexahydro-1H-azepine-1-carbothiolate; biphenylethers such as 2,4-dichlorophenyl-4'-nitrophenylether and 2,4,6-trichlorophenyl-4'-nitrophenylether; benzothiadiazines such as 3-isopropyl-1H-2,1,3-benzothiadiazin-(4)-3H-one 2,2-dioxide; anilides such as 3',4'-dichloropropionanilide, oxadiazolines such as 2-t-butyl-4-(2,4-dichloro-5-isopropyloxy
• the herbicide of this invention is suitably applied either preemergently or postemergently to the growth medium or to the plant, e.g., to the soil or the flooded area after the transplant has been fixed.
• the active ingredient is suitably applied at a rate of about 0.05 to about 4 or more lbs. per acre (i.e., from about 0.06 to about 4.48 or more kgs/hectare).
• a preferred application range is from about 0.25 lb/acre to about 1.5 lb/acre (i.e., from about 0.28 kg/hectare to about 1.68 kgs/hectare), and the most preferred and usually recommended use rate is about 0.5 lb/acre (about 0.56 kg/hectare).
• the amount of herbicide used is dependent upon the organic content of the soil. This is within the knowledge of those skilled in the art.
• herbicidally effective amounts of the active ingredient, N-(butoxymethyl)-6'-tert-butyl-2-chloro-o-acetotoluidide, or its admixture with other herbicidally-active compounds are dispersed in or on soil and/or applied to aboveground or flood-water portions of plants in any convenient fashion.
• Application to the soil or growth media can be carried out simply by admixing with the soil, by applying to the surface of the soil and thereafter dragging or discing into the soil to the desired depth, or by employing a liquid carrier to accomplish penetration and impregnation.
• liquid and particulate solid herbicidal formulations to the surface of soil or above-ground or flood-water portions of plants can be carried out by conventional methods, e.g., power dusters, boom and hand sprayers and spray dusters.
• the formulations can also be applied from airplanes as a dust, a spray or granules because of their effectiveness at low dosages.
• the distribution of the active ingredient(s) in soil can be carried out by admixture with the water employed to irrigate or flood the soil. In such procedures the amount of water can be varied according to the porosity and water-holding capacity of the soil to obtain the desired depth of distribution of the herbicide.
• soil as employed herein is intended in its broadest sense to include all conventional "soils” as defined in Webster's New International Dictionary, Second Edition, Unabridged (1961).
• soil refers to any substance or media in which vegetation may take root and grow, and is intended to include not only earth, but also compost, manure, muck, humus, sand and the like adapted to support plant growth.
• plant means dormant seeds, germinant seeds, germinative seeds, emerging seedlings and established vegetation including the roots and above-ground portions.

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• Life Sciences & Earth Sciences (AREA)
• Agronomy & Crop Science (AREA)
• Pest Control & Pesticides (AREA)
• Plant Pathology (AREA)
• Health & Medical Sciences (AREA)
• Engineering & Computer Science (AREA)
• Dentistry (AREA)
• General Health & Medical Sciences (AREA)
• Wood Science & Technology (AREA)
• Zoology (AREA)
• Environmental Sciences (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)

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Cited By (3)

Citations (2)

• 1974
  • 1974-07-12 US US05/488,096 patent/US3955959A/en not_active Expired - Lifetime
• 1975
  • 1975-05-27 PH PH17196A patent/PH16993A/en unknown
  • 1975-06-30 JP JP50080759A patent/JPS5126224A/ja active Pending

Patent Citations (2)

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